| I-League | 10.01.19 | Churchill Brothers | - | Gokulam Kerala | 3:1 |  |
 |
||
| I-League | 26.01.20 | Gokulam Kerala | - | Churchill Brothers | 1:0 | |
|||
| I-League | 08.03.20 | Churchill Brothers | - | Gokulam Kerala | 1:2 | ||||
| I-League | 16.03.22 | Mohammedan SC | - | Churchill Brothers | 1:2 | |
|||
| I-League | 06.05.22 | Mohammedan SC | - | Churchill Brothers | 2:0 | |
|||
| I-League | 06.12.22 | Churchill Brothers | - | Mohammedan SC | 2:1 | ||||
| I-League | 07.02.23 | Mohammedan SC | - | Churchill Brothers | 1:2 | ||||
| I-League | 19.03.25 | Dempo SC | - | Churchill Brothers | 1:3 |
Trinité-et-Tobago